


A-Z: NSFW Edition

by faequeentitania



Category: Supernatural
Genre: A-Z, Affection, Anal Sex, Barebacking, Bondage, Bottom Dean, Bottom Dean Winchester, Bottom Dean Winchester/Top Sam Winchester, Bottom Sam Winchester, Character Study, Choking, Cock Tease, Come Eating, Come play, Coming Untouched, Cuddling & Snuggling, Cum Play, Cunnilingus, Dean in Panties, Fellatio, Female Sam Winchester, Ficlet, Fluff, Fluff and Smut, Gags, Gender or Sex Swap, Holding Hands, Lazy Mornings, Lazy Sex, Light BDSM, Love, M/M, Magic, Marijuana, Mirror Sex, Morning Sex, Multiple Orgasms, Mutual Masturbation, Oral Sex, Overstimulation, Panties, Pet Names, Porn Watching, Quickies, Recreational Drug Use, Rimming, Romance, Sex Toys, Sex on the Impala, Shotgunning, Teenchesters, Top Dean Winchester, Top Sam Winchester, Topping from the Bottom, Vibrators
Language: English
Status: Completed
Published: 2016-04-28
Updated: 2016-10-05
Packaged: 2018-06-05 02:22:32
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 26
Words: 17,145
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6685420
Author URL: https://archiveofourown.org/users/faequeentitania/pseuds/faequeentitania
Summary: <blockquote class="userstuff">
              <p>An A-Z of sexy Wincest headcanons in story format. A love song of Dean's worship of Sam. <a href="http://fairy-tail-babes.tumblr.com/post/127326718826/headcanon-game-a-to-z-nsfw">Click for the prompt list that inspired this.</a></p>
            </blockquote>





	1. A = Aftercare

**Author's Note:**

> I haven't done a writing challenge for a while, and I really liked this [NSFW headcanon ask meme](http://fairy-tail-babes.tumblr.com/post/127326718826/headcanon-game-a-to-z-nsfw), so I decided to turn them into story format prompts. All ficlets.

They don’t talk about it. Dean’s pretty sure he would punch Sam in the face if he tried to bring it up in the light of day, and he’s fairly confident Sam knows that.

So they don’t talk about it. But it definitely happens. And secretly, it’s one of Dean’s favorite things. It’s almost better than the sex itself, which is probably the most ridiculous thing he’d ever thought in his life. Considering his life, that’s an astronomically high rating.

Doesn’t change the fact that it’s true. It’s the after that Dean _really_  loves. Orgasms are _insanely good_ , don’t get him wrong, but after all that is said and done, he gets almost as high just from touching Sam; no sexual intent at all.

When the sex is really good, when it’s really intense (after a near-miss, after a really good day, after hours of flirting and teasing), Sam sometimes trembles. Over exertion, over stimulation, Dean’s not sure what, but it makes him want nothing more than to put his hands all over his brother; stroke every spasming muscle and caress every jittering bone.

He gets lost in it; the feel of Sam’s damp skin against his hands or his lips, the warmth of their bodies, the sound of Sam’s breath slowly calming. He loves it, loves when Sammy returns the touch, his huge, gun-calloused hands stroking over Dean’s skin in a gentle massage.

Sex is good. Sex is friggin’ _great_. But it wouldn’t mean half as much if they didn’t have the after; when every touch was a silent way to say ‘I love you.’


	2. B = Body Part

Dean’s got killer lips. It’s a fact that he knows; he’s gotten more compliments on how pretty his mouth is than anything else since he hit puberty.

Sam is no exception to its effects. Dean will test him, sometimes. Toy with a fork or spoon during dinner, sliding it in and out of his mouth until he gets that hungry look in Sam’s features. Or he’ll order a Belgium waffle just as an excuse to get a shit-ton of whipped cream, licking it from his lips obscenely while he watches Sam squirm. He freakin’ _loves_  candy canes around Christmas; it’s the best ammunition he has all year to get Sam hot and bothered.

Yep, he’s got an awesome mouth, and he knows it.

Then there’s Sam. It’s hard to pinpoint any one specific feature about Sam that he loves more than the others; Sam’s just… _Sam_ , beautiful and tall and strong.

But if he absolutely _had_  to pick, Dean would go for Sam’s hands. Not that he’d ever admit it to his giant ‘little’ brother, but Dean loves the fact that Sam’s hands are just so _huge_. It makes him feel protected, in some way, when Sam cups his face to kiss him and his hand almost spans the entire distance from Dean’s chin to the tip of his ear.

Maybe it’s something to do with the fact that he knows exactly what those hands are capable of; has seen them do so much violence, inflict pain and injury. Yet he’s choosing to touch Dean with gentleness instead, or passion, or desperation. Dean feels safe, in those hands. He feels good, in a way they aren’t really good at expressing with words.


	3. C = Cum

**Notes for the Chapter:**

>  **Warning:** this is straight up filthy- includes cum play and rimming post-unprotected sex. You’ve been warned. It’s also 881 words, which almost falls outside ficlet territory but whatever.

“Fuck, _fuck_ ,” Dean growled, tightening his grip on his cock, his hand moving fast and slick. He was fucking _close_ , if Sam would just…  


He groaned as Sam manhandled his leg a little further up, his brother’s face buried in his neck and Sam’s dick buried in Dean’s ass. With each frantic stroke of his cock the back of Dean’s knuckles brushed Sam’s stomach where they were pressed close together; sweaty and hot and _so fucking good_.

Dean gasped at Sam changed pace; his fast, eager thrusting suddenly becoming deep and hard and exactly right where Dean needed it.  
Sam nailed his prostate dead-on once, twice, three times and Dean was coming, intense and hard and all over his stomach with a breathless sound.

And Sam, Jesus, he just kept going, just kept hitting Dean where he was sensitive inside until he thought his whole body was going to fly apart with the intensity. Weakly he held on, the hand he had in Sam’s hair going tight and the other scrabbling against Sam’s abs, not pushing away, not yet, but just flailing uselessly for some way to hold on through it.

Finally Sam grunted, pressed in deep and held himself there, grinding tight little hitches of his hips that took Dean’s breath in little spasms.

“Jesus,” Dean gasped as the last of Sam’s orgasm faded, leaving his over-sized brother weighing heavy and boneless on top of him, “ _Jesus_.”  


“Yeah,” Sam breathed dreamily, nuzzling into his neck with gentle licks and kisses that were making Dean’s whole body twitch, “Fuck that’s good.”  


Dean gave a breathless little laugh, “Damn right, my ass is awesome.”

Sam just chortled in reply, pressing a kiss against Dean’s still-rapid pulse.

He was hot, and sticky, and would _definitely_ need a shower after all that, but Dean also felt insanely, bone-meltingly good.

Until Sam pulled out, mostly soft now, and Dean became acutely aware of how sloppy and wet he was.

“Ugh,” he scowled, “Jesus, Sammy, are your balls inside out from all the jizz you just dumped in me?”

Sam made a disgusted face, looking at Dean like he was an unpleasant chore he had to endure, “Do you _have_ to be gross all the time?”

Dean shrugged with a waggle of his eyebrows, and Sam sighed, shaking his head.

“You’re lucky I love you,” he sighed, swooping in for a kiss before Dean could protest the “chick-flick moment.”

Sam got up on his knees between Dean’s spread legs, stroking up his thighs in a way that made Dean’s muscles quiver. Sam looked at him pensively, his thumbs stroking little circles on the inside of Dean’s knees and Dean raised his eyebrows imploringly, “Dude, what?”

“You are a mess,” Sam acknowledged, reaching out and pressing his palm flat to Dean’s abdomen, where his cum was still laying tacky and opaque on his skin. Idly Sam rubbed at it, smearing it over Dean’s belly before tracking his hand lower.

Any witty retort Dean would have had promptly died as Sam’s fingers dipped behind his balls and traced his hole, smearing the dripping mix of cum and lube around the rim. He shivered, his nerves still sensitive, and a little smirk tugged at the corner of Sam’s lips.

“Fuckin-!” Dean grunted at Sam pressed two fingers in, pushing in deep and rubbing at his insides, making him shake with sensitivity.  


Dean wasn’t sure whether to be relieved or annoyed when just as quickly Sam’s fingers retreated, coming out shiny and slick with cum. Dean groaned as Sam touched his abdomen, swirling his fingers in dizzy patterns through Dean’s cum, combining them filthily.

“Jesus Christ, Sammy, you kinky fuck,” Dean grinned, and Sam smirked.  


Suddenly Sam was hauling his hips up in the air, and Dean gasped as his shoulders dragged several inches across the bed.

“What-” he started to ask, then cried out in shock as Sam pushed his tongue into Dean’s ass, the relaxed muscle offering no resistance to the intrusion.  


“Holy Jesus fuck,” Dean gasped, flailing for anything to hold onto as the most obscene sounds of licking and slurping made his face flush.  


Sam’s hands held him tightly in place as Dean’s body trembled and writhed, and Dean himself wasn’t sure if he was trying to get away or get closer; the hot wet press of Sam’s tongue licking at him incredible and too much at the same time.

“Fuck, stop!” Dean gasped, a crazy, fluttery motion of Sam’s tongue feeling like a sucker punch to his nervous system; he was on the verge of circuit overload that was edging uncomfortably toward pain.  


Thankfully Sam listened, giving one last, filthy lick inside him before letting Dean’s hips down gently onto the bed. Dean stared dazedly at the wide swipe of slick across Sam’s mouth and down his chin, and Sam smirked as he wiped the back of his hand across his mouth salaciously.

“Kinky fuck,” Dean gasped again, trembling a little and Sam pressed down over him again with a grin, nuzzling at Dean’s neck affectionately like he hadn’t just eaten out Dean’s cum-sloppy hole.

“Love you too, baby,” Sam purred, sarcastic little fuck that he was, and Dean cuffed him weakly on the back of the head.  


“Shut up, bitch.”  



	4. D = Dirty Secret

Rhonda fucking Hurley. He never would have thought that a girl named _Rhonda_  would be one of the sexiest experiences of his life. She was cute and plush and flirty as hell, and Dean had zero hesitation in bringing her over while Sammy was at school for some freakin’  _amazing_  sex.

It would be an understatement to say Dean learned _a lot_ about himself that afternoon. He learned exactly how much he liked to be pushed around in bed, for one. Give him orders, manhandle him, ride him like he’s a toy to be driven hard and put away wet and he’s putty in his partner’s hands. He doesn’t like to think too hard about what could have attributed to that little hard-wiring quirk in his brain, but he doesn’t suppress it, either. Life’s too short to not enjoy whatever the fuck you want in bed.

But the goddamn _panties_. Pink and satiny and batter-fried _wrong_  but holy fuck was it hot. Dean was perfectly aware, however, that that was a little more niche than being submissive in bed.

It’s not that he hasn’t _tried_  to bring it up with Sammy, in his own, roundabout way. It’s just… tricky. The panties thing… well, it was a little too personal, a little too far into Dean’s pocket of vulnerability, so if Sam thought it was weird or gross it would probably do a bit more damage to Dean’s ego than he was comfortable risking.

Still, he’s allowed to _look_ , allowed to _imagine_ , at any rate. He’s tested the waters a few times, while they picked up a few odds and ends at some random all-night Walmart or some such place.

“Whatcha think, Sammy?” he’d say, holding a pair of baby blue, lacy panties across his hips and smirking. Inside, his heart was going triple time, “Suits me, don’t ya think?”

Sam would inevitably roll his eyes, scoffing at Dean’s waggling, suggestive eyebrows.

“Put them back, idiot,” Sam would chuff, “Make yourself useful and do some _actual_  shopping, alright?”  


Rinse and repeat, with only slight variations from state to state, Walmart to Walmart. So Dean kept his dirty little secret for now.


	5. E = Experience

**Notes for the Chapter:**

> I don’t care what “Bad Boys” said, there is no way that Dean “Sex on Legs” Winchester didn’t get kissed until he was 16. Shut up

Dean’s been told his whole life that he’s a charmer. Little old ladies, waitresses, hotel clerks; all he has to do is smile and compliment and he’s got them in his pocket. He intuitively learned the right body language, the right tone of voice, the right amount of teeth to show in a smile and a laugh.

When he was a kid, he used it to get extra of the free samples at the supermarket, or con a kind old grandma at the corner store to buy him and Sam popsicles.

When he was 14 he used it to get a kiss from Sarah McNalley under the bleachers. When he was 15 he used it to get under Teresa Rizzi’s cheerleader blouse in a closet during a game of 7 minutes in heaven. When he was 16, he used it to get into Rita Smithson’s panties in the truck bed of her father’s Ford.

He perfected it, over the years. Everyone says that Sam’s the brainiac in the family, and may be that’s true about some things, but Dean would be willing to bet significant money that he’s master when it comes to women. And that’s not just ego, he’s put in the work to learn. Charming your way into someone’s knickers in one thing, making it worth their while (and a repeat invitation) is another. Dean has mastered both due to practice and research, thank you very much.

Which is why he felt a little out of his depth the first time he found himself being pressed against a motel wall with Sam’s big body caging him in and kissing the hell out of him. He didn’t quite know what to do with the hard, thick press of dick against his hip, even as his own responded enthusiastically in kind. (It didn’t help that they were royally drunk when it happened, either.)

But they adapted, and learned, and practiced. Dean may not have as large of a sample size when it comes to dicks vs pussy, but he hasn’t heard any complaints from Sam. On the contrary, he’s personally seen Sam blackout from coming so hard, so he thinks it’s pretty fair to say that he’s mastered this whole gay sex thing just as much as he mastered hetero sex.

What can he say? Dean doesn’t half ass it.


	6. F = Favorite Position

Call Dean a sap, but he liked being face to face. Didn’t much matter to him the arrangement otherwise; whether he was getting fucked or doing the fucking, on top or on his back. Either way, he wanted to have hands-on access to his partner.

Touching was the point, after all. Running his hands over them, feeling their skin, pressing his mouth to them for a kiss or a nip; it all just made it better for them and for him.

And there was just so much of Sam to touch. A beautiful, broad back that curved gracefully to a narrow waist, thick, muscled arms, strong runner’s legs, a throat that just begged to be kissed and bit. Not to mention that ridiculous hair; he ribbed Sammy all the time about it, he just couldn’t resist the temptation. But honestly, he loved it; it was silky and soft and Sam was so _reactive_ whenever Dean played with it. A gentle stroke with his fingers followed by a tight grip timed just right could make Sam cream himself in an instant.

He wouldn’t give any of that up in exchange for any crazy positions they could find in the kama sutra. No, call him a sap, but he’d rather have Sammy in his arms; all Dean’s to stroke and hold and kiss.


	7. G = Goofy

**Notes for the Chapter:**

> Takes place after "The Chitters". Because I couldn't resist.

“Dude, we have got to do this more often,” Dean giggled. They were lying in bed, and Sam was currently swiping obscenely good licks of his tongue over the sensitive flesh of Dean’s neck.

“Hear me?” He asked, petting Sam’s hair, “We gotta do this more.”

Sam chortled, coming up for air and nuzzling Dean’s cheek, “What, do a Weed Sampling Tour across Colorado like those girls?”

“Yes!” Dean nodded enthusiastically, “Fuck yeah! Dude, do not deny that you feel awesome right now.”

Sam giggled then, full on rubbing his cheek gently against Dean’s like a big cat, “Yeah,” he sighed dreamily, “Yeah, feels good. Doesn’t mean we should do it all the time though. Still illegal in Kansas, not worth the trouble.”

Ok, Sam was way too cognizant if he was able to rationale all of that.

“Here,” Dean murmured, reaching for the ashtray on the bedside table. They were on their second joint, which had extinguished itself when they started fooling around, but Dean now plucked from the little notch on the side where they had wedged it, “Have another hit and tell me that we shouldn’t do this again.”

Sam chortled again, but pulled back, holding the joint while Dean fumbled for his zippo, “M'not saying never again. Just saying not where it’s illegal. Not worth the trouble of getting it.”

Dean flicked the zippo open and lit it, holding it up for Sam to light. Dean was a little mesmerized by way Sam’s cheeks hollowed as he sucked the smoke in, and was proud when his little brother didn’t cough this time.

Sam pulled back when it was sufficiently lit again, holding his breath. Dean smiled with pride.

“Well don’t just sit there hoggin’ it, gimme,” he complained after a moment, motioning for the Sam to pass over the joint.

Sam smirked instead, holding it away and leaning his head down instead, pressing his lips to Dean’s and nudging his lips open.

_Fuck that’s hot,_ Dean thought dizzily as he cottoned on to what Sam wanted, and immediately pressed up into it, sealing their mouths together as Sam gently blew the smoke into Dean’s mouth.

Dean breathed deep, the smoke a dull burn in his lungs and Sam’s lips soft and sweet against his.

Sam pulled back, watching Dean, and Dean held the smoke in as long as he could before breathing out in a quick huff.

He grinned, reaching for the joint again and this time Sam let him take it. They did it again, this time from Dean’s lungs to Sam’s, and several times more after that, back and forth.

When the joint was burnt so low it was hot against Dean’s fingers they quit, tossing it in the ashtray to burn itself out.

Sam was still hovering above him, just staring at him with half-lidded eyes and Dean smiled.

“So pretty, Dean,” Sam murmured after a moment, leaning down and rubbing their noses together, “So, so pretty.”

“Pretty too, Sammy,” Dean answered, feeling very much like he was melting onto the bed he was so relaxed, “Come on, kiss me, let’s fuck.”

Sam moaned, nodding a little, then eagerly pressed their lips together. It was an uncoordinated and lazy kiss, but it made Dean groan nonetheless, turned on and happy.

He felt Sam’s hand at his zipper, and slid an uncoordinated hand of his own down to help. A few false starts and they got there, shoving jeans and underwear down and off, then doing the same to Sam.

“Hello,” Sam giggled, scooting down the bed and putting himself at eye level with Dean’s dick, “Gonna lick you now.”

Dean laughed at the fact that Sam was quite clearly talking directly to Dean’s cock, but didn’t complain as Sam licked a sloppy line from the base of Dean’s dick to the tip. He laved his tongue around the head like he was licking a lollypop, and Dean groaned breathily, still smiling like a crazy person.

“Show it how much you love it, Sammy,” Dean purred, “Come on, baby.”

“Mmm, so much,” Sam slurred, opening his mouth and sucking Dean down, hot and wet and really _really_ nice.

“Mmm, good puppy,” Dean grinned, “Use your tongue, baby, come on.”

Sam pulled off, giggling.

“You called me puppy?” He grinned, licking his lips, “I can be puppy.”

With a silly smile he went back to it, licking Dean’s dick with sloppy, broad strokes of his tongue.

Dean chuckled, playing along and stroking Sam’s hair like he was petting a dog, “Good boy,” he encouraged, “Suck me off good, puppy, and you can fuck me like a bitch.”

Sam groaned at that, looking up at Dean through his lashes and Dean’s cock twitched at the sight.

“Yessir,” he husked, sucking Dean’s cock back in his mouth and Dean groaned.

“Good boy.”


	8. H = Hair

Dean learned the importance of being well-groomed early on. What it basically came down to was that girls were less willing to do certain things if they found important aspects of your body less than appealing.

Thankfully, he inherited the more fair features of their mother, which for him meant what body hair he had was very light and blond; a trait he found readily acceptable to most of the people he tried to bed.

There were still certain things he maintained, of course. Any hair below his belt, primarily.

He didn’t completely shave down there (had tried it, and while it had its certain appeals, he didn’t love it enough to keep up with the hassle), but he kept it all trim and neat.

As far as he was concerned, it was only fair, if he was going to ask someone to put their mouth there.

Which he did, somewhat frequently. Thankfully Sam didn’t seem to mind, as there was little that thrilled Dean the way Sam looked when he was on his knees, that smart mouth of his stuffed full of cock. It was an even trade off, in his opinion, as Sam seemed equally fond of ploughing Dean into the mattress; and sometimes being one orgasm ahead just made the whole process of being split on Sam’s dick go smoother and easier.

He couldn’t deny either that having sparse body hair was an advantage when both partners involved in the sexy times produced semen. Waking up with it dried and crusted on your body was less unpleasant if you didn’t have to deep-scrub it from a crazy bush of pubic hair. A gross but true fact of life that Dean had just come to accept.


	9. I = Intimacy

**Notes for the Chapter:**

> Jesus Christ is this mushy and 1200 words please forgive me.

Dean doesn’t like to admit it, but he’s a romantic.

Not in a grand gestures or constant gifts kind of way. Especially with Sam, he cringes at the very thought. But definitely in the way that made Dean want to spend all day in bed with his brother, watching TV and snuggling into the comfy warmth of Sam’s body.

Or in the way that made him want to come up behind Sam when he was eyeballs deep in books and research and give him a massage, working the stiff muscles of Sam’s back until he was relaxed and leaning back into Dean’s touch.

He was romantic in the way that made him pull Sam close to him when they were driving down long stretches of boring road with hours to go. He’d tug on Sam’s shirt, make him slide over on the bench seat until they were hip to hip, thigh to thigh, and Dean could rub mindless circles over Sam’s knee with his thumb while Sam draped an arm around his shoulders. Or sometimes Sam would lay down sideways across the seat, his head pillowed on Dean’s lap and Dean would stroke his hair until he fell asleep.

Mostly he was romantic in a way that made him want to do things for Sam, just because it was something that made Sam happy, or made his life easier or more comfortable.

Stopping at a Salad Works instead of a greasy burger joint. Letting Sam pick the movie. Giving him first shower after a messy hunt. Letting him sleep in while Dean made breakfast, then bringing him coffee in bed to wake him up.

It may not be other people’s definition of romance, or how they portray it in the movies; but for them, acts like that could be as good as a bed of rose petals and champagne by candlelight.

“I like it when you’re like this,” Sam confessed once, spooned up against Dean’s back in the middle of the afternoon and some cowboy movie they had seen a hundred times playing low in the background.

“Hm?” Dean asked, half asleep. He was full of pizza and beer from lunch, and the warmth of their bed was lulling him fast toward a nap.

“I like this,” Sam said again, soft and quiet, “I like it when you just want to spend time with me.”

“Sammy, all I do is spend time with you,” Dean chuckled, “We’ve lived together for almost 30 years, remember?”

“You know what I mean,” Sam murmured, pressing his face into the back of Dean’s shirt and Dean’s heart tightened.

“I know, Sammy,” he answered, putting his hand over Sam’s where it was wrapped around his waist and interlacing their fingers. Sam’s fingers flexed tightly around his for a moment, “I like it too. You know I do.”

Sam nodded, pressing a kiss to Dean’s back; Dean shivered a little at the hot puff of breath that clung to the fabric of his shirt.

“Come ‘ere,” Dean murmured, shifting around, and Sam loosened his hold to let Dean wiggle onto his back, “Come ‘ere, Sammy.”

Intuitively Sam understood, moving over him, and Dean spread his legs to let Sam settle between them.

Sam’s arms slid under him and Dean sighed contently at the way his hands curled over the top of Dean’s shoulders, holding tight and occasionally squeezing in a gentle massage.

Dean wrapped his arms around Sam’s neck in turn, pulling him down for a thorough kiss.

It was so easy to get lost in it; sharing breath, sharing a kiss, sharing the warmth and the feel of their bodies. Barely any time at all for Dean to start aching with want, his hips pressing up into Sam’s answering hardness. He fumbled for the hem of Sam’s shirt, hiking it up until he could feel bare skin and tracing the beautiful stretch of muscle that was Sam’s back.

Sam helped him get it completely off before returning the favor, getting them chest to chest with nothing between them.

Dean smoothed his hands over Sam’s hair, taming the tasseled strands, just looking at each other. Sam pressed in close again, his mouth hovering over Dean’s, their lips just barely touching.

Dean shivered as Sam worked one hand down his side, thumbing the jut of his hip bone before moving inward toward Dean’s cock. He squeezed it gently through the fabric of Dean’s boxers, and Dean’s breath hitched in his chest.

“Can I?” Sam asked breathily, hand dipping lower, and Dean shivered when Sam traced his hole with his fingers; a firm pressure that made Dean’s hips jolt.

“Fuck. Yeah, Sammy, do it,” Dean panted, reaching down and pushing at the elastic waist of his boxers. Sam helped, and between the two of them and some shuffling, they managed to finally get naked together, the feel of skin-on-skin blissfully good in its simplicity.

“Do you need…?” Sam’s fingers traced his rim, sending sparks through his nervous system, but Dean shook his head.

“M'good, Sammy,” he encouraged, “Just want you, c'mon.”

“Yeah,” Sam breathed, pressing their lips together in a messy kiss, “I got ya, Dean. I got ya.”

Sam reached for the lube on the bedside table, flipping the cap and angling it with one hand to tip some into his palm. He brought the hand to his dick, slicking it up and Dean pressed his mouth to Sam’s neck distractedly.

“C'mon Sammy,” Dean encouraged again, “M'ready, c'mon.”

Sam guided himself to Dean’s hole and pressed in in a steady push. Dean trembled at the feel of it, panting against Sam’s neck. His body was still relaxed and eager from the first round several hours ago, and the slide in was nothing but good.

“Ok?” Sam asked anyway, holding still and waiting for Dean.

“Don’t stop,” Dean answered, wrapping his legs around Sam and pulling him in eagerly. Sam groaned as he sank in to the hilt, and Dean squeezed his muscles around Sam encouragingly, “Don’t stop, Sammy, give it to me.”

“Yeah,” Sam breathed, pressing their mouths together as he finally started to move, sliding his arms under Dean and holding tight as his hips picked up a steady rhythm.

Dean loved it like this. Plastered tight together, able to feel each breath in Sam’s lungs, the beat of his heart, their skin getting slick with sweat and his cock rubbing dirty and eager against Sam’s abs. He could never be close enough to Sam; could never satisfy the aching, deep need for his brother that sat deep in his chest and just wanted _everything_. But in moments like this, they came close.

Then Sam just shattered him, made the chasm of Dean’s love break open in his heart when he freed one hand and grabbed Dean’s own, lacing their fingers together and pressing their joined hands into the pillow right beside Dean’s head.

It was such a simple gesture, but in the moment it was like Sam had reached inside his chest and took hold of his heart instead, and he just came apart. He gasped and groaned against Sam’s mouth, shaking his way through orgasm and Sam followed in an instant; pushing in deep and hard and unforgivingly good.

They didn’t move for a long time. When they did, their hands were the last thing they let go.


	10. J = Jack Off

**Notes for the Chapter:**

>  **Warning:** Features underage sexuality (Mid-teens). There is no actual sexual contact between said underage people, but there is ample mutual masturbation and the watching of lesbian porn. You have been warned.

Dean likes to pretend that he hasn’t been in love with Sam for as long as he has. It’s a self-preservation thing; a way to convince himself that he didn’t permanently damage Sam’s psyche when they were growing up.

But the truth of the matter is, they’ve been five steps away from normal brothers for a really long time. For starters, they slept in the same bed for far longer than most people would deem socially acceptable. Their life on the road occasionally had something to do with that, but when given the option of two separate beds and their dad the next room over, they still chose to share for most of their childhood.

It just felt safe, felt like home, when they would share a mattress. To this very day, Dean will always get a better sleep, feel more rested and peaceful, when Sam is sleeping with him.

Even when that stopped, when Dean was 14 and realized that other people just didn’t do that, it didn’t change the fact that they were more intimate than any brothers should be.

And maybe Dean encouraged that, a little. But Sam was his everything; his only friend, his only sibling, his only playmate, his only confidant. It didn’t seem weird, at the time, to share everything with Sam, even the really nitty-gritty stuff.

It’s not like Sam didn’t _know_ what was going on. The kid was always whip-smart and inquisitive, it didn’t take him long to figure out exactly what pay-per-view was all about, and why people watched it.

It just became another thing that they did together; another check box in their shared life, their shared routine.

Dean liked it, he looked forward to it. Which should have been a red flag, but he was young and stupid and horny. So picking out a porno with your baby brother and getting off together; totally fine by his teenage standards. They were going to be racking up the pay-per-view bill anyway, might as well both enjoy it and get the most bang for their buck.

“That one,” Sam said decisively, and Dean chortled, but selected it anyway.

“I’m noticing a pattern, here, Sammy,” Dean smirked as the video started, “Getting a bit of a thing for lesbians, huh?”

“Shut up, jerk,” Sam snorted, “Don’t see you complaining.”

Dean wasn’t, not by a long shot, but it was fun to rile Sam up sometimes.

“Just sayin’, Sammy, careful it doesn’t turn into a fetish. Not being able to get your rocks off without mouth-breathing over lesbians would be a tough gig.”

Sam threw his extra pillow at him.

“Just shut up and watch the fucking movie, Dean.”

Dean cackled, but finally shut up. It was a typical porno; bad dialogue, worse acting, stupid plot and cheap sets. But the girls were pretty and it didn’t take them long to get to the good stuff.

Dean rubbed his cock through his boxers, just teasing himself, amping up for when things got really good. Out of the corner of his eye, he could see Sam doing to the same; just rubbing his thumb over the head of his cock, tiny shivers passing through his little brother with each stroke.

 _“Yeah, fuck, baby, lick me good,”_  one of the girls moaned, exaggerated and loud, but Dean ignored it in favor of watching the brunette on the screen do as she was told, getting to her knees on the floor beside the sofa and pressing her face into the blonde’s pink pussy.

A little moan from Sam, and Dean had to agree. The brunette was _enthusiastic_ , to say the least, and it wasn’t long before Dean lost the will to keep his hands outside of his boxers.

With a moan of his own he got his dick out, stroking firm but slow from base to tip. Dean wasn’t the type to rush; he much preferred a long, hard orgasm over a fast but fleeting one. Too many of those in crap, weak-water pressure showers, thank you very much. If he was watching porn, he wanted it to be _good_.

The blonde was really into it now, and Dean knew at least half the noise she was making was exaggerated and over the top, but if the flush on her chest and neck were anything to go by, at least she was actually enjoying it. He liked to see that in porn; it bored him to death when the actors would focus more on trying to look sexy than actually enjoying and participating in what was going on.

Apparently it was working for Sam too; Dean could hear the quick stokes from Sam’s bed, his brother’s soft panting and the quick _snick_ of precome being smeared down Sam’s shaft with every stroke. That was a shared trait, Dean had discovered. Get them turned on and their cocks drooled precome like a leaky faucet.

 _“Shit, yeah!”_ the blonde cried out as the brunette pulled a dildo from somewhere, sliding it in and fucking her with it like a machine, her tongue still licking obscene and wet on her clit.

Dean’s hand sped up of its own accord, and even he was breathing quick now, precome oozing out his slit and running hot and and slick down his shaft; smeared around by his stroking hand.

“Fuck,” Sam panted, and Dean couldn’t help but look over, Sam’s hand a blur on his dick and his brother arching as he started to come.

Every intention Dean had of holding on a bit longer went out the window at the sight of it, and completely against his will he came, watching Sam instead of the screen.

“Shit,” Dean panted, wringing the last spurts of cum from his cock and finally letting his eyes close.

“Yeah,” Sam agreed, and Dean opened his eyes again. Sam was looking at him now with heavy-lidded eyes and flushed, sweat-shiny skin.

“Wanna keep going?” Sam asked with a grin, “There’s still 45 minutes left. Think you can get it up again, old man?”

Dean returned the grin, looking back to the screen, where the two women where now 69-ing.

“You’re on, babyface.”


	11. K = Kinks

**Notes for the Chapter:**

> I am out of control with these word counts, so much for this being a ficlet challenge. **Warning:** Bondage ahead.

By any rational means, Dean shouldn’t like this. This was something that should be associated with pain and panic, not pleasure.

But the first time things got truly rough, when Dean put up a struggle with a smirk and a goad and challenged Sammy to _make me_ , Dean ended up shoved face first onto the floor, Sam’s hands bruising his wrists and the power of Sam’s thrusts inside him jolting his whole body against the floor. He ended up with rug burn on his _dick_ for Christ’s sake.

And he’d never come harder in his life. Being in Sam’s hands like that, pushed and manipulated and _pinned down_ ; it shouldn’t be hot. But _fuck_ , it was.

Then Sam asked about rope. Held it in his hands and asked _Please, can we just try? Any time you want to stop, I’ll stop, I promise you. But… can we?_

He just looked so _earnest_ ; the fucking puppy dog eyes and nothing but love on his lips. Dammit, he couldn’t deny this man anything.

It shouldn’t be this good. In their line of work, rope didn’t mean anything good. Monsters used rope. Hunters used rope. Rope meant chafed skin and strained joints and cut off circulation. Rope never meant pleasure.

Damn if Sam didn’t do his research, though. Each rope and knot meticulously placed around Dean’s wrists, perfectly tied to keep Dean where Sam wanted him, but not to hurt him.

It was awkward at first; Sam too apprehensive and Dean too unsure, but then something just clicked. By the end of it, Dean was pretty sure he had momentarily gone blind with how hard he came.

They were quite a few steps away from that first, nerve-wracking time, and it just kept getting better and better.

He was confident that this time wasn’t going to be any different.

Instead of apprehension, Dean felt nothing but excitement and anticipation when Sam finished the last bit of knotting at his wrists. Immediately he tested them, pulling and twisting his arms to try to escape. No avail, and Dean smiled in affirmative.

Sam answered it with a smile of his own, immediately getting onto the bed and kneeling on all fours over Dean. It was a gorgeous sight; Dean drank in the view of Sam’s sculpted chest, trailing down to his sharp hip bones and hard, heavy cock.

Dean welcomed the kiss Sam pressed to his mouth, humming softly with a pleased sound. That’s all Sam did, at first. Just kiss, the two of them making out like teenagers in the backseat of a car.

Dean got lost in it, just enjoying the simple pleasure, and it wasn’t until he instinctually tried to slide his hands into Sam’s hair that the ropes came back into sharp focus.

Sam chuckled, murmuring against Dean’s mouth, “Forgot, huh?”

“Shut up,” Dean mumbled, and Sam chuckled again, pulling back and ignoring Dean’s whine of protest.

“Stop bitching,” Sam told him, “Or I’ll find another use for that mouth.”

Dean shivered, but remained silent. Not that he would object to Sam using his mouth, but he found that Sam’s plans were so much better when they went uninterrupted by Dean.

“Good boy,” Sam grinned, leaning down and pressing another kiss to Dean’s lips. Then there was that. Compliments from Sam always made him uncomfortable; too many self-esteem and self-doubt issues that got in the way, but somehow hearing _that_ particular praise made him melt into a submissive little puddle.

“Thought we might try something different today,” Sam said lowly, stroking a gentle hand down Dean’s bare chest. He stopped to thumb one nipple distractedly, and Dean twitched.

“And what’s that?” Dean asked, arching into Sam’s touch, begging for more.

“How would you feel about me riding your cock like this, hm?” Sam asked with a flirty smirk, and Dean groaned breathlessly, dick twitching hard at Sam’s words.

“Yeah,” he breathed, “Yeah, Sammy, I’d be cool with that.”

Sam laughed, straightening up over him. He combed his fingers through his hair, pushing it out of his face and his eyes running over Dean.

“I don’t even have to touch you, look at you,” Sam purred, looking at Dean’s dick salaciously. A sticky drop of precome slid torturous and hot down Dean’s shaft, and it twitched again under Sam’s gaze, “You’re ready to blow just thinking about what I’m going to do to you.”

Dumbly Dean shook his head and pulled at the ropes, trying to will himself to calm down, despite how fast his heart was beating and how every word Sam said just strung him tighter with want. Sam was right; he was going to snap, and hard.

Sam grinned, seeing right through him, “Guess we won’t waste time, then,” he said decisively, wrapping his hand around Dean’s dick and guiding it between his legs.

Dean had a moment of shock and confusion before he sank inside, and Sam’s head titled back on a moan.

“Fucking fuck,” Dean groaned, his own head thrown back and his hips jerking up into that incredible, tight heat. He had no idea when Sam had taken the time to prep, but _holy fucking shit_ this was one of the hottest things his brother had ever done.

“Fuck, that’s good,” Sam groaned, ass flush with Dean’s hips, and he just rocked for a moment; his muscles squeezing and relaxing as they adjusted to Dean’s cock.

Dean pulled hard on the ropes, panting like crazy and trying mindlessly to get his hands on Sam’s hips. He needed Sam to _move_ dammit; he needed those deep, hard thrusts that drove Sam just as crazy as they drove him.

Sam leaned down, pressing a hard, dirty kiss to Dean’s mouth before _finally_ starting to move properly; bracing himself on Dean’s chest and rising his hips slowly up before slamming back down.

It was hard and fast, and _so fucking good_ Dean could do nothing but moan. He scrabbled to plant his feet on the bed, which momentarily threw Sam off rhythm, but he recovered quickly; Dean’s thrusts up as Sam slammed down making Sam cry out in pleasure.

“Sammy, Sammy, I can’t-” Dean whined, rushing toward the edge and no way to stop it. Sam just reached for his own cock, jerking it tight and fast and angling his hips just right to make it count where Dean was thrusting hard inside him.

Dean cried out as he was suddenly thrown over the edge, coming hard and blindingly good deep inside Sam’s body. His hips ground up, riding it as long as he could; the feel of Sam’s tightening, flexing muscles around him milking him for all he was worth.

A handful of seconds later and Sam came with a hard grunt, his hot cum splattering thick and heavy all over Dean’s belly and chest.

Dean pried his eyes open through the last throws of his orgasm to watch; drinking in the sight of Sam’s arm muscles bulging and flexing as he jerked himself hard and fast, his abs tight with pleasure and his sweaty hair half covering his face as spurt after spurt of hot white cum covered Dean’s chest. The sight just ratcheted Dean up to eleven, the last throes of his orgasm overwhelmingly intense and if there was ever a time that someone’s brain melted out of their ears, it was in that moment.

The next thing he was aware of was Sam’s hands around his wrists, and he could feel the ropes steadily loosening. Finally they were free, and Sam cradled his wrists in his big hands, stroking over the rope burn that was sure to be there for days.

“We need to start wrapping your wrists,” Sam murmured, slowly bringing Dean’s arms down, mindful of his stiff muscles, “That’s gonna be painful.”

Dean gave a non-committal grunt. He liked the marks; something to remind him of the rope nights every time he looked at them. They’d talk about it later.

Sam’s mouth pressed to his, and he barely had the strength to kiss back; his whole body felt like a cooked noodle and he was pretty sure his brain had been turned into oatmeal.

“I love you,” Sam whispered soft and low, and Dean didn’t have the strength to be flustered about it. It was a phrase Dean still had difficulty with, macho bullshit and fear still fighting to stay rooted in his head despite Sam’s best efforts to the contrary.

Dean just angled his head up for a kiss instead, and freed his wrists from Sam’s grasp to take Sam’s hands, pressing them against Dean’s chest.

Sam understood, and they shared soft kisses until Dean fell asleep, one of Sam’s hands still pressed over his heart.


	12. L = Location

Practically, beds were the best. They were comfy, there was plenty of space, nice cozy blankets. In a lot of ways, it was Dean’s favorite place to have sex. It just had the most advantages, and the added bonus of being able to get a good night’s sleep afterwards.

But in his heart of hearts, nothing made him hotter than fucking in the Impala.

The familiar smell of the leather, the feeling of home, how goddamn beautiful she was. She was right up there next to Sammy in his heart, and combining those two things (his brother and his car) made any day better, in Dean’s view. Throw sex in the mix and he was on cloud nine.

Now that they have their own garage, it’s even better. It’s private, it spacious, they can be as loud as they want and go for as long as they want, with no prying eyes or risk of arrest.

All of which allows for Dean’s favorite thing; not just sex _in_ Baby, but sex _on_ her. Being spread out on her hood and fucked boneless and stupid is one of the great pleasures in Dean’s life, hands down.

Thankfully, Sam at least gets it. He’ll tease about Dean having a car fetish, ask him if he’d rather be alone with Baby for some private time; but at the end of the day, Sam loves the car too, and he gets it.

Dean’s favorite is when they’re washing the car. Dressed down, just a t-shirt and jeans (or shorts, as has become Dean’s favorite) and Dean can put on a bit of a show. He’ll lean far over the hood, t-shirt riding up and ass pushed out, letting his clothes get all wet and giving Sam a flirty smirk.

Sam inevitably laughs, sliding up behind him and taking hold of Dean’s hips. He’ll press in close, draping himself over Dean and kissing his shoulders as his hands trace Dean’s sides.

“Hope you have lube in those cute little shorts,” Sam will always tell him, like Dean hadn’t been preparing for this all day. He does, of course, seducing Sam is always half the point of recruiting him to wash the car.

There’s just something about it. Sam pushing Dean’s shorts down his hips and bunching his shirt up to his shoulders. The cool metal against his front while Sam presses hot and solid against his back. Holding onto the hood up at the hinges, near the windshield, as Sam fucks hard and deep into him and makes him see stars.

He even likes the ritual after, of washing his cum off his Baby and actually finishing washing the car; relaxed and well fucked and wet as hell, but that’s the beauty of it. He can be all those things, he can finish washing the car that way, and be able to corner Sam in the shower after; wash the sweat and the suds off and try to coax Sam into another round pressed against the tile.

Beds are nice, but being able to do all of _that_ … Dean will take the garage any day.


	13. M = Motivation

When you’ve known someone almost the entirely of your life, you would think you’d start to become desensitized to some of the things they do.

Apparently Dean, for whatever reason, does not really fit into that category. Sam’s puppy eyes, created and perfected from the age of three, still guilt Dean into doing what Sam wants. Whether that thing is convincing him to go with Sam’s plan on a hunt, or to help him do laundry, or to _please, just do this for me? I promise I won’t bug you about food for a week, just please eat something healthy today, ok?_

Always, every damn time, he ends up doing what Sam wants. It really is a ridiculous, unfair advantage and Dean does not appreciate it.

By that same token, though, there are things that Sam does that drive him crazy in all the best, sexy ways. Things that Sam’s been doing for years that still get him hot, still make him want to jump Sam’s bones right then and there.

By all rational means they should have lost at least a bit of their effectiveness by now. But nope, Dean’s just as hooked as he was ten years ago, no sense of waning in sight.

When Sam gets excited about something is his favorite. That eager, giddy look he gets when he geeks out is just too precious for Dean to resist.

A close second to that is Sam in FBI mode. Sam has the incredible ability to present himself as either mellow and unnoticed or as the most impressive person in the room, and when he does the latter, Dean has a very hard time keeping his hard-on under control. Throw the suit in on top of that and he has to focus very hard on remaining professional.

And those are just the things Sam does in their general lives that get Dean hot for him. When Sam’s purposefully _trying_ to seduce him is a whole other ballgame.

Sometimes Sam will just get this calculating look and his whole demeanor will change; he becomes FBI, “get shit done” Agent Smith that can silence a room with this very presence. The difference is that it will be focused entirely on Dean, and Dean will lose his capacity for concentration almost instantaneously. Those nights are the ones Dean privately refers to as “Power Nights”; when Sam gets pushy and rough and becomes this power dom eager to put Dean in his place.

Dean _loves_ those nights.

Other times Sam is just a tease; waiting for Dean to crack and come to him. Fleeting touches and flirting, but never pushing; just waiting for Dean to get impatient and demand Sam’s attention.

Which he readily gives, once Dean’s asked for it. Those nights are softer, more about affection than straight lust but Dean loves them just as much, even if he doesn’t want to admit it. Those nights, instead of being pushy and in control, Sam’s all about the give and take.

He’ll take his time, be gentle with Dean just because they can and he knows Dean likes it. It becomes a slow burn that ends in fireworks rather than the fast track.

It’s often miraculous to Dean, the fact they can still do so much to turn each other on, even after all this time together. He’s never bored, which is more than most long-term partners can say. He’s pretty lucky, in that regard.


	14. N = No

Sam’s never pushed a limit that was too far for Dean. They’ve tried stuff Dean wasn’t sure he would like, but it was never anything that made him balk and question Sam’s sanity or anything like that.

Dean chalked it up to them just having pretty similar tastes.

Over the years, they’ve talked about different things that they’ve tried, what they liked, what they didn’t, what they’ve seen in porn that they’d want to do and things they wouldn’t.

They’re in 100% agreement about bodily fluids boundaries. Anything that isn’t spit or semen is never anything they would want to purposefully include in their sex life.

They’re not really keen on doing it anywhere risky or weird, either. I mean sure, they’ve done it in a few bar bathrooms, the car, even occasionally in a graveyard after an easy salt and burn. But they’re not really interested in the risk of getting caught, or causing trouble over it. Not when there are plenty of other more opportune (and comfortable) places.

Once Dean’s little… _interest_ for BDSM-flavored activities came to Sam’s attention, they had a pretty thorough discussion about it. It wasn’t as awkward as Dean feared it would be, and was actually pretty insightful into the things Sam was into and not into as well. He was pretty pleased his brother’s tastes ran more exciting than he originally thought.

Light-hearted teasing was fine, actual degradation and humiliation was not. Dean didn’t mind dropping the occasional “sir” in the mix when Sam would give him orders, but that was pretty much the only formality he would feel comfortable using. “Master” was just too much, and they both had way too many parent issues for the “daddy” dynamic to be even remotely appealing.

Dean liked a bit of pain with his pleasure, but nothing beyond what Sam could do with his hands; slapping, scratching, pinching. Any combination of the above was cool in moderation, and thankfully Sam wasn’t the sort to get hyped up on the idea of actually hurting Dean, which worked well for both of them.

Other than those hard and fast rules, Dean was a pretty adventurous type. To his surprise, Sam was too, and it always made Dean’s day to pull some new, sexy quirk out of Sam’s head.

Trying them out was even better, and Dean had a growing list scribbled in a notebook that they were always crossing off and adding to as the opportunity arose.

As Dean became fond of saying, you gotta get your kicks where you can.


	15. O = Oral

Dean _loves_ oral sex. It’s quite possibly his absolute favorite type of sex, both giving and receiving.

It’s just so intimate. Getting up close and personal with someone’s junk just isn’t something you can phone in.

Oral was the mainstay of his first sexual fantasies. He stole his first skin mag at the tender age of 12, and out of all the images that besieged his hormone-seeped brain, the sight of a brown haired beauty with her lips around a cock, staring seductively up at the camera, hit him the hardest.

He jerked off to that picture for months; until the creases in the page literally fell apart and he had no choice but to bin it. Not long after that, he was daring enough to delve into the world of video porn, and that’s when his love for it _really_ took root.

No longer was it just a still image on a page; it was _sound_ and _movement_ , and Dean spent many a morning shower wank thinking about it. 

And _Sam_ , Jesus, he’s a fucking champ. Dean loved oral before, but when Sam got on his knees for him for the first time, he just about exploded it was so hot.

What makes it all even better is how much Sam loves it too. How quick he is to kneel between Dean’s spread thighs and press his mouth to the front of his big brother’s jeans, just because Dean wants him to.

Sam likes to tease, like that. Just rubbing his mouth back and forth over the bulge against Dean’s fly, breathing hot and humid against the fabric.

He won’t move on until Dean is squirming, his hands buried in Sam’s luxurious hair and his breath quick with anticipation.

He’ll wait until Dean is cursing and bitching about his annoying tease brother before Sam will _finally_ unfasten his jeans and pull him out. He’ll waste no time after that, thank god, and Dean relishes that first, sinful plunge into Sam’s hot wet mouth.

Some days, Sam gets him off fast and dirty like that. Tonguing and sucking with every trick he knows to get Dean to come apart, just because he can.

Other days he draws it out for ages, bringing Dean to the edge over and over but not letting him get off. Not until Dean’s cock is flushed red and desperate, and Dean’s all but crying in frustration.

But it’s ok. Dean returns the favor, when it’s his turn. Turnabout is fair play, after all. Dean isn’t complaining; he loves it.


	16. P = Pace

Dean’s a sensual person. Every other aspect of his life is rough and hard, so he likes to leave that behind when he steps into the bedroom.

It’s weird to him that Sam leans more in the opposite direction. But to each their own, he supposed. They were willing to compromise, and it worked well for them.

It depended on the day, really. Some days Dean was just as eager for the fast and rough as Sam was, and some days Sam was nothing but soft and gentle.

Ideally, their day would include both.

Even more ideally, more than once. 

They didn’t always have the leisure of doing so. More often than not, they barely had time to sleep, let alone enjoy each other. It made it all the more important when they could, hence why Dean was a fan of taking it slow and sensual, touching and making Sam feel good as much as possible.

It worked for them. Compromise.


	17. Q = Quickie

“Dean,” Sam said warningly, “What are you doing?”

Dean grinned, pressed against Sam’s back in the tiny motel bathroom. Casually he reached around and palmed Sam’s morning wood, causing his brother to tense and grab his wrist with a disappointed frown.

“Dean!” Sam said again, “Dude, come on, we have to meet with the sheriff in less than an hour.”

“Better be quick, then,” Dean smirked, squeezing gently and pulling a gasp from Sam’s throat, “Think if I fuck you just right, I can make you come in under five minutes, little brother?”

Dean’s cock gave a twitch as he watched Sam’s reflection in the bathroom mirror, and his brother’s pupils visibly dilated. He could see the inner battle going on inside Sam’s head at the proposal, and he squeezed Sam’s cock a little more firmly.

“Five minutes,” Sam finally assented, releasing Dean’s wrist and Dean pressed a kiss to his shoulder to hide his smile.

Roughly he pulled Sam’s boxers down to mid-thigh and kicked his legs apart, pushing Sam forward and forcing him to brace himself against the wall, hands on either side of the bathroom mirror. A glance at Sam’s reflection told him exactly how much Sam was enjoying it, his brother’s dick fully hard and Sam’s eyes watching hungrily in the mirror.

Quickly he pulled out the tube of lube he had put in the elastic waistband of his own boxers, squirting a liberal amount onto his fingers before tossing the tube into the sink.

“How much do you need?” Dean asked huskily, grabbing one of Sam’s perfect asscheeks in one hand and rubbing one slick finger at Sam’s hole with the other.

Sam shook his head on a shaky breath, pushing his hips back into Dean’s hands eagerly, “Not much. Just make it slick.”

Dean groaned at that, his hips churning restlessly with want, and he nodded. Topping Sam was never anything but intense. His brother’s taste for the rough stuff turned him on fiercely, but scared the crap out of him too. Hurting Sam went against every instinct he had, but seeing what it did to him, how hot it got him, how hard it made him come; Dean couldn’t say no to that.

Dean pressed two fingers inside Sam on a hard thrust, and Sam cried out, head tilted back and dick leaking drips of precome into the sink. It was positively sinful how fast Sam could get hot like this.

“Good?” Dean panted, hand tightening on Sam’s cheek and fingers working in and out steadily, the luscious flutter of Sam’s muscles gripping his digits.

“Yeah,” Sam panted, “Yeah, come on, do it.”

Dean trusted Sam at his word, and released his ass to reach into the sink for the lube, fingers pushing in deep and rubbing hard against his prostate.

Sam groaned loud and hard at that, pushing back into the hard rub, and Dean smirked, kissing Sam’s shoulder as he switched to tight, firm circles that made Sam shake.

“Fuck, Dean, hurry up,” Sam whined, and Dean flipped the cap on the lube, pulling his fingers out and squirting a healthy dollop into his palm. He slicked his cock with a quick but thorough swipe, then grabbed Sam’s ass and parted his cheeks to expose his flushed hole.

He guided his cockhead to press against the rim, the muscle fluttering at the pressure, “Good?”

“Good,” Sam huffed, “M'good, go.”

“Slut,” Dean teased with a soft laugh, pressing in steadily and watching Sam’s face in the mirror.

Sam’s eyes slammed shut and he lowered his head, his hair covering his face, and Dean knew he was hiding a grimace of discomfort. Yet when he looked down, Sam was still rock hard and dripping precome into the sink, and the groan he let out when Dean’s hips pressed flush against his ass was nothing but a good sound.

“Ok?” Dean asked anyway, holding still, and Sam growled as he pressed back against Dean and pulled one hand from the wall to stroke himself.

“Fuck me, come on,” Sam demanded impatiently, and Dean knew better than to ask twice.

Sam groaned again as he started up a quick rhythm, and Dean watched hungrily in the mirror as his brother continued to stroke his cock, his temporary discomfort melting quickly into nothing but pleasure.

“Come on, baby,” Dean panted against Sam’s neck, wrapping his arms around Sam’s chest and snapping his hips hard. He knew he got it just right when Sam started shuddering, moaning and pushing back into it and stroking his cock fast and tight.

“Fuck, fuck,” Sam gasped, and Dean watched transfixed as Sam started to come, his abdomen tensing and his hand a blur on his cock. Pulse after pulse of cum spurted through Sam’s fingers, and it was so pornographic and filthy Dean buried himself deep and came hard, sinking his teeth into Sam’s shoulder and groaning.

They panted together for a few moments after, and Dean kissed the red indents his teeth had left in Sam’s skin.

“That was definitely more than five minutes,” Sam husked after a moment, and Dean chortled, “We’re gonna be late.”

“Not if we share the shower,” Dean offered helpfully, rubbing his hand in a small circle on Sam’s chest, “Come on, Sammy, I’ll even wash your back.”

Sam looked up and met his eyes in the mirror, and Dean was proud of the pleasure-glazed look he found there.

“You’re an idiot,” Sam muttered fondly, and Dean grinned, smacking Sam’s ass and enjoying how his brother jumped.

“That’s the spirit, Sammy.”


	18. R = Risk

**Notes for the Chapter:**

> No, I haven't forgotten about this. I've just been busy moving from New Jersey to Georgia, so my life has been a sea of cardboard boxes for the last week and a half. Back on track with a masturbation and choking fic!

“There’s something I want to try,” Dean said, fiddling nervously with his beer bottle.

Sam paused with his own beer half way to his lips, looking at Dean with a quirked eyebrow.

“Ok…?” Sam prompted, bringing his beer the rest of the way up to his mouth and taking a swallow.

Dean waiting until he was done before speaking.

“Choking.”

He expected the look of surprise and apprehension, and waited patiently as Sam took another drink of beer.

“That’s…” Sam said finally, then blew out a quick breath, “I don’t know, Dean.”

“I trust you.“

“It’s not a matter of trust,” Sam sighed, “It’s a matter of risk. Choking isn’t like me tying you up and getting a bit of rope burn and some welts. We’re talking about your airway, your arteries, your vocal chords. That’s a level of delicate I don’t think I want to mess with.”

“Squeeze here,” Dean said simply, putting his own hand up to his neck and pressing against the valleys on either side of his windpipe, “It puts pressure on the arteries, slowing the blood flow to the brain. Same light-headed feeling of restricted oxygen without actually depriving me of oxygen.”

Sam looked taken aback, like he hadn’t expected Dean to have done any research on the matter. He bit his lip, thinking.

“It still makes me nervous,” he said at last, and Dean’s heart sank, “So if you really want to do this, we start simple.” 

It took a second for Dean’s brain to catch up with what Sam said, but when it did, his eyes widened.

“Really?” he asked eagerly, “I mean, yeah, absolutely, simple it is. What did you have in mind?”

“Finished?” Sam asked, nodding at Dean’s beer, and Dean quickly downed the rest in several quick swallows.

Sam chuckled as he did the same, then stood, looking around thoughtfully. Dean followed his lead, standing up and waiting for Sam to tell him what to do next.

Finally Sam nodded, then indicated for Dean to sit back down. He did, already getting hard in anticipation.

Sam came around and knelt on the floor in front of him, the guy so damn tall that even on his knees he was almost eye level with Dean.

“Giant,” Dean grumbled, and Sam chuckled.

“You love it,” he murmured in return, leaning in and pressing a kiss to Dean’s lips, his hands on Dean’s thighs.

Dean slid his fingers into Sam’s hair, angling his head into the kiss and giving a soft hum of contentment.

Gently Sam’s hands stroked, trailing up and down Dean’s thighs leisurely and coming just close enough to Dean’s zipper to be a tease.

Dean shifted in his seat, eager for Sam’s touch where he really wanted, but Sam kept it innocent; just stroking over Dean’s thighs and occasionally squeezing his knees.

“Get your dick out,” Sam instructed in a low murmur, and Dean shivered, immediately reaching for his own belt.

“Good,” Sam hummed, pulling back and licking his lips as he looked at Dean’s flushed cock. Dean knew that look, and he gripped the arms of his chair with an eager breath.

Sam smirked, glancing up at Dean’s face before ducking down to take Dean in his mouth, sucking deep and tight in one graceful motion.

Dean groaned, tangling his fingers in Sam’s hair and just holding on as Sam laved his tongue against the head.

“Fuck, Sammy,” Dean sighed, eyes fluttering closed and head titling back. Sam continued to suck, head bobbing slow over his cock and making pleasure crawl up and down his spine.

Sam’s hands started to move, trailing up his thighs and over his hips, then gentle and slow up his abdomen and chest. Dean shivered as Sam reached his neck, one hand curling over his shoulder and the other tracing gentle over his throat.

Sam pulled off his dick with a wet sound, turning his head to wipe his mouth on the fabric of his sleeve.

“Come ‘ere,” he said huskily, hand curling around Dean’s jaw and pulling him down, angling him for a messy kiss. Dean went eagerly with a little whimper, fingers tightening in Sam’s hair.

“Touch yourself,” Sam commanded with a growl, pulling back and putting his hand around Dean’s throat.

Dean trembled with a groan, releasing one hand from Sam’s hair and wrapping the other around his wet cock. He began to stroke as Sam’s hand tightened.

Sam watched his face intently, but Dean’s eyes couldn’t help but flutter closed as he slowly started to feel the effects of Sam’s hand around his throat.

“Ok?” Sam asked softly, and Dean nodded, his head starting to feel a little lightheaded.

“Tap out if it gets too intense,” Sam reminded him, and Dean nodded again.

Sam’s hand went a little tighter, and Dean was panting, his blood pounding in his ears and in his cock, pleasure tingling all over his skin.

His hand worked faster, and he could feel his orgasm sneaking quick and intense up his spine as spots started to swim behind his eyelids.

He gave a hoarse whine as suddenly pleasure punched him in the gut and he came, hard and intense and all over himself in messy spurts.

Suddenly Sam released the pressure on his neck and blood flooded back to his head, the intensity increasing tenfold and he almost passed out it was so good.

Next thing he knew, Sam was stroking his hair with one hand and holding him upright with the other, Dean’s face pressed against his shoulder.

“Still with me?” Sam murmured softly with a light chuckle, and Dean gave a non-committal grunt.

He felt loose and limp, and his head still a little fuzzy. Slowly he motivated himself more upright, and Sam cupped his cheek to look intently at his face and neck.

“I don’t think you’ll bruise,” he said after a moment, and Dean nodded. His throat felt slightly sore, but nothing that he thought would last long.

“So I’m guessing that was good?” Sam smirked, and Dean chuckled breathily.

“You could say that,” he murmured with a grin, “What about you?”

“That was…” Sam bit his lip, “Hotter than I thought it would be.”

“See?” Dean grinned a little wider, “Told you.”

“Shut up.”


	19. S = Stamina

**Notes for the Chapter:**

> This one fought me tooth and nail for some reason, and I have no idea why. Finally shook the whole 1,052 words out because apparently I’m a runaway train with word counts.

Dean was shaking. He wasn’t going to last much longer, not like this. Not with the way Sam was pinning his wrists to the bed and panting hot against his throat, his cock pegging perfect-good against Dean’s sweet spot.

“Fuck, Sammy, slow down,” Dean gasped, body writhing uselessly as each hard pound of Sam’s hips sent sparks down his spine.

“Not a chance,” Sam purred, licking a hot, wet stripe along Dean’s throat, “Want you to come just like this.”

Dean groaned, his body threatening to make good on Sam’s words embarrassingly easily.

“Asshole,” Dean panted, then cried out as Sam screwed his hips in hard, grinding steady and merciless inside him.

“Come on, sweetheart,” Sam whispered soft against the shell of his ear, and Dean couldn’t hold on any longer if his life depended on it.

With an almost pained sound he came, hard and intense and shaking like a leaf in Sam’s hands.

“There you go,” Sam groaned, grinding in deep with hard, erratic hitches of his hips that Dean swore he could feel in his throat, “There you go, baby.”

Dean would have complained about being called “baby” if he had even a fraction of his brain cells left functioning. As it was, he was strung out and limp and still trembling through hard pants of breath as Sam’s thrusts gentled to a steady, slow in and out.

“Gonna keep on, just like this,” Sam whispered softly, trailing his lips along Dean’s cheek to his mouth, “You’re gonna come for me again.”

A tender kiss against Dean’s slack lips and he whimpered, exhausted at the very idea.

“Can’t,” he breathed, muscles spasming and another whimper pulled from his throat as Sam angled his hips, digging into his over-sensitive prostate with the head of his cock.

“Yes you can,” Sam assured him in a low timbre, easing up, but just barely, “You’re going to come until you come dry tonight.”

Jesus. On a good day, Dean was no slouch in bed. He knew how to make it last, make it good for everyone involved. But _Sam_ ; he was some kind of zen master when he put his mind to it. He could twist Dean into pretzels and pound him into the mattress until the elder Winchester’s brain turned to mush, and Sam would just hold on and hold on and _hold on_ until Dean was begging him to _come already, you stupid asshole_.

It looked like tonight was going to be one of those nights.

“Want you t'come too,” Dean slurred dazedly, “C'mon Sammy, want you t'come.”

He squeezed his inner muscles as best he could, arching his chest up and squeezing Sam’s waist with his thighs. Sam’s breath hitched and his grip on Dean’s wrists tightened. Dean felt a flutter of satisfaction.

“C'mon, Sammy…” he murmured again, rubbing his cheek against Sam’s and squeezing again, “Want you to, c'mon…”

He could feel Sam’s control slipping; the uneven, jittery thrusts of his hips and the shuddering panting in Dean’s ear crystal clear signs. Sam was always a sucker for Dean’s voice, especially the fucked-out and breathy way Dean sounded when he was riding high on endorphins.

“Cheater,” Sam growled, pulling back up on his arms and setting a punishing pace, making Dean’s breath catch in his throat.

“Fuck, please, Sammy,” Dean groaned, twisting with jolt after jolt of pain-pleasure bursting up his spine as Sam abused his sensitive prostate, “Sammy…!”

Almost against his will his cock started to throb and thicken, hardening between them and Sam smirked.

“Good boy,” he growled, and Dean whimpered, squeezing his inner walls as tight as he could and shaking at the intensity. Sam was going to pull another orgasm from him, he could feel it in the tingle at the base of his spine. But so help him, Sam was going over the edge with him if it was the last thing he did.

Suddenly Sam released one of Dean’s wrists, reaching between them and wrapping a tight grip around Dean’s cock. Dean cried out, back bowed and breath caught in his throat; passing out was a strong possibility that he knew Sam would never let him live down.

“Come on, Dean,” Sam growled, “Come for me, baby, come on.”

Desperately Dean reached for Sam with his one freed hand, sliding his palm up Sam’s arm and over his shoulder until he reached his head. Roughly he tangled his fingers in Sam’s hair, gripping hard as Sam worked his palm roughly against the tip of Dean’s cock.

One hard thrust just right and Dean was coming again, whole body locking up as his orgasm was pulled ruthlessly from him by Sam’s merciless touch.

“Good boy,” Sam panted, and Dean growled as he pulled hard on Sam’s hair with the last bit of strength he had.

“Fuck fuck!” Sam gasped, and Dean could feel him coming too, Sam’s hips jerking in tight and hard as he was finally pulled over the edge.

“Cheater,” Sam panted again, trembling above Dean as he rode out the last pulses of pleasure.

Dean didn’t even hear him, so blissed out and exhausted that his whole body shook and hurt with overstimulation.

Wordlessly Sam lowered himself back down over Dean, putting them chest to chest and pressing his face against Dean’s gently.

Dean wasn’t sure how long Sam was calling his name before he was cognizant enough to realize it, but once he did he barely had the strength to open his eyes in answer.

“Did I hurt you?” Sam asked softly, and Dean realized that Sam was dragging his thumb through the tear tracks running from the corners of Dean’s eyes. He didn’t even know when that had happened, and he swallowed thickly before he could assure Sam’s anxious, concerned face.

Instead of speaking he shook his head minutely, then leaned into Sam’s hand, closing his eyes again and trying to will the trembling in his limbs to stop.

“Ok,” Sam breathed softly, pressing a kiss to Dean’s slack lips, “Ok.”

Dean must have fallen asleep immediately after, because the next thing he was aware of was feeling clean and warm, with Sam tucked up behind him as the big spoon.

Too tired to do anything else, he snuggled back against Sam and let himself drift back to sleep.


	20. T = Toy

**Notes for the Chapter:**

> Welp, another 1200 word smut-a-thon.

“Seriously?” Dean asked with a grin, rubbing his calf against Sam’s under the little motel table flirtatiously, “Never?”

“Shut up,” Sam blushed, but pressed back against Dean's leg anyway.

“But come on,“ Dean laughed, rolling his beer bottle between his hands. His ring made a satisfying clicking noise against the glass, “Have you never stepped foot in a sex shop? Or ordered anything online?”

Sam flushed a deeper red and mumbled something Dean didn’t catch.

“What?” He nudged, kicking Sam under the table.

“Ow!” Sam said indignantly, kicking him back, “I said no, alright? I just never saw a need to.”

Dean chortled, shaking his head, “It’s not about _need_ Sammy, it’s about _fun_.”

Sam shrugged, spreading his hands and Dean smiled wider.

“Strip,” Dean commanded, standing up abruptly. Sam looked at him with raised eyebrows.

“What?” Sam asked with confusion, and Dean impatiently came around to his side of the little table.

“Strip,” he repeated, pulling at Sam’s shirt, “We’re fixing that. Right now.”

“I- wait, what?” Sam asked incredulously, “You have sex toys?”

“Aw,” Dean smiled, leaning down and placing a kiss on Sam’s lips, “How oblivious.”

“No but seriously, since when? How have I not stumbled across them before?”

“Because I’m not an idiot, Sam,” Dean sighed impatiently, “I don’t just leave them lying around. Now are you gonna get naked or what?”

Sam blushed another adorable shade of pink before standing up and stripping off his shirt. Dean smirked and went for the buckle on Sam’s belt, undoing it rapidly as he pressed in for another kiss and started pushing Sam toward the bed.

A gentle push to Sam’s beautifully broad chest and he sat, helping Dean with his pants and boots before moving further back onto the bed and laying down.

“Why am I nervous?” Sam suddenly asked, running an anxious hand through his hair, “It’s just you, why is this weirding me out?”

Dean chuckled, stripping off his own clothes with practiced ease, then getting on the bed and crawling over Sam on all fours.

“Because,” he murmured as he leaned down for another kiss, “You’re not used to me knowing more than you.“

Sam chuffed, reaching up and stroking his hands over Dean’s shoulders and neck and pulling him down for another kiss, “That’s definitely not true.”

“Sure it is,” Dean shrugged, “It’s ok, Sammy. You’re the brains and I’m the muscle, it’s just how things shook out.”

Sam sighed and shook his head, cupping Dean’s face gently and giving him a look that Dean couldn’t quite interpret.

“Let’s stop talking about this right now,” Sam murmured, suggesting that Sam actually had quite a lot to say on the matter. Dean cringed a little internally, “You were bragging about sex toys earlier, let’s see these magic orgasm gadgets of yours.”

Dean chuckled, sitting up and clapping Sam on the thigh with a smirk, “Oh you innocent scoop of vanilla, you have no idea.”

Sam kicked him gently as Dean got off the bed, mind churning over what exactly he wanted to use on Sam first. He settled on simple but intense.

With a flourish he dug out a vibrator. It was thin and long but with a fat, bulbous head curved just right to make Sam scream. 

Snagging the lube as well, Dean came back to the bed with a smirk on his face, watching Sam’s expression.

“I can’t believe I didn’t know you had this,” Sam wondered again, hiking himself up on one elbow and reaching out to touch it with his fingertips. Dean chuckled.

“Lay back,” he instructed, nudging Sam’s knees apart and settling in, placing the toy on the bed beside him.

Sam obediently did as he was told, watching Dean with interest.

With a wink and a smirk Dean slid his hand around Sam’s cock and bent down to take it into his mouth. Sam made a little noise of surprise, reaching for Dean and stroking his fingers through his brother’s short hair. He was barely hard, but Dean would fix that soon enough.

A few deep, hard sucks and he could feel Sam thicken and harden in his mouth. With a pleased hum he reached for the lube, flipping the cap and squeezing a generous amount onto his fingers before dipping them between Sam’s cheeks and against his hole.

Sam gave an encouraging little moan, hiking his legs up higher to give Dean better access. Dean willingly took advantage, pressing a finger inside slowly as he flicked his tongue against Sam’s slit.

“Fuck, that’s good,” Sam breathed, hand tightening on the back of Dean’s skull, and Dean smirked with satisfaction.

It was easy to work Sam up like this, one finger quickly going up to two, and Dean spread his digits wide inside Sam and listened to his brother’s eager moans.

Satisfied that Sam was loose enough, Dean pulled out and slicked the toy with lube. Sam stilled, panting lightly and quivering with anticipation.

Dean pulled off Sam’s cock with a wet noise, pressing the fat head of the toy against his hole and watching his brother’s face.

“You good?” He husked out, just teasing it at Sam’s entrance, and Sam nodded.

Slowly Dean pressed it in, working it in little pushes until they were past the thickest part and it slid the rest of the way in on an easy glide.

“Fuck,” Sam murmured, squirming a little and Dean just smirked.

“You ain’t seen nothing yet, Sammy, just you wait,” he purred, pushing it in and out slowly, going a little deeper each time. Gently he angled it, pushing and…

“Yatzee,” he grinned as Sam jolted, groaning as it did exactly what it was meant to do; nudging up good and tight against Sam’s prostate.

Dean kept it there, varying the pressure and the force of his thrusts as Sam panted and writhed.

With no warning to Sam, he clicked it on.

Sam cried out as the vibrations started up, his big hands grabbing desperately at the sheets as his cock twitched and precome oozed from his slit.

“That’s it, baby,” he cooed, rubbing it tight and firm against Sam’s sweet spot and watching raptly as Sam jerked and moaned. His own cock was heavy and throbbing between his legs, and he groaned as he finally wrapped a hand around it.

Slowly he amped up the power, the vibrations getting more intense and Sam getting more and more wanton.

“That’s it, baby,” Dean encouraged again, finally cranking it up to the highest setting and pressing it tight to Sam’s prostate, “That’s it, baby, come on.”

Sam cried out, grinding hard against the pressure and Dean nearly lost it as Sam’s back bowed and he came untouched all over his stomach.

“Fuck, Sammy, fuck!” He groaned, keeping the toy pressed tight and intense inside Sam until Sam was scrabbling desperately for Dean’s hand and pushing him away.

Dean withdrew the toy and replaced it with his cock in one smooth motion, burying himself to the hilt and thrusting a handful of times before he came, riding the spasmy aftershocks of Sam’s orgasm with a groan.

“Oh my fucking god,” Sam moaned, low and exhausted and Dean gently lowered himself over Sam with a breathy chuckle.

“Told you,” he panted, pressing a string of open-mouthed kisses to Sam’s chest.

Sam stroked his hair, giving another little moan, “Fuck, I’ve never come like that before.”

“It was fucking hot,” Dean growled, nipping at Sam’s chest, and Sam chuckled.

“Guess you’ll just have to do it more often.”


	21. U = Unfair

**Notes for the Chapter:**

> Damn, I was not feeling this one _at all_. I’m throwing in the towel; this is the best I could do.

“You fucking ass,” Sam growled, and the second the door was closed behind them Dean found himself pressed against the wall, Sam’s big, imposing body closing him in and Sam’s hands tangled in the front of his shirt.

“That’s not very nice, Sammy,” Dean smirked, tilting his head back against the wall and looking at Sam through his lashes sweetly.

“Neither was your little grope session under the sheriff’s desk when you were supposed to be acting like a fucking professional,” Sam fumed, and Dean smiled wider.

“It’s the suit, Sammy, it does things to me,” Dean purred, wrapping his hands around Sam’s hips and giving a little squeeze, “Besides, I had to keep up both awake through that’s sheriff’s droning monotone. He sounded like the teacher from Ferris Bueller, I was doing us both a favor.”

Sam’s bitch face intensified, and Dean smiled a little wider.

“On your knees,” Sam suddenly growled lowly, pulling Dean away from the wall and pushing down on his shoulders roughly, “You’re going to finish what you started.”

“Yessir,” Dean purred.

Sometimes Sam was just too easy.


	22. V = Volume

“Jesus, Dean, shut the fuck up,” Sam hissed, biting at the back of Dean’s neck. Dean whimpered, nails digging into the flesh of Sam’s arm where it was wrapped around his waist.

“Thought- _ah!-_ thought you liked me loud,” Dean panted, muscles tightening and shaking as Sam’s cock in his ass and his hand on Dean’s dick flooded his whole body with pleasure.

“Not when Bobby’s next door,” Sam growled, digging his hips in hard, and Dean couldn’t help the yelp it ripped from his throat as it nailed his prostate dead-on.

“Jesus, Dean!” Sam gasped, releasing Dean’s cock to clamp a hand over his mouth, and Dean groaned; both at the loss of touch to his dick and the musky, bitter smell of his precome on Sam’s hand.

“I’m going to fucking gag you if you don’t quiet down,” Sam threatened in a low growl, and Dean moaned, dick twitching at the thought.

“God, you’d love that, wouldn’t you?” Sam huffed with amusement, “Should I start pricing ball gags?”

Desperately Dean released his grip on Sam’s arm to wrap his hand around his dick, precome dripping onto the sheets as Sam’s words painted a mental image in his head.

“Slut,” Sam laughed quietly in his ear, hand tightening around his mouth. Dean moaned again, mindlessly licking and mouthing at Sam’s palm as he wound tighter and tighter with arousal.

“Maybe I should get one of those ones that hold your mouth open instead,” Sam gasped, hips speeding up and thrusting harder, forcing a litany of whimpers and moans from Dean’s throat, muffled against Sam’s hand, “Keep you quiet by stuffing your mouth full of cock.”

“Yes, yes!” Dean whined, the words completely muted by Sam’s palm. Suddenly Sam’s weight was heavy on his back, pushing him forward as Sam thrust hard and desperate, close to the end.

It pushed Dean’s head into the pillow, Sam’s grip over his mouth tightening and the press of the pillow almost cutting off his air. That’s all it took for Dean to come, whining and thrashing as he spilled hot and thick into his palm.

Sam’s teeth sank into his shoulder, muffling the deep groans as he came a moment later.

Dean jerked his head out of Sam’s grasp, gasping and panting as Sam licked the indents he had left in Dean’s shoulder sweetly.

“Kinky, Sammy,” he giggled breathlessly, and Sam nipped at him with a chortle.

“You’re the one who just got off thinking about me gagging you,” Sam pointed out, and Dean could hear the smile in his voice.

“And you’re the one who thought of it, don’t pretend like you weren’t into it, bitch.”

“Shut the fuck up, jerk.”


	23. W = Wild Card

**Notes for the Chapter:**

> Holy crap I’m finally updating this??? Amazing! This Wild Card theme is MAGIC SEX.

Dean knew he really should have been more worried, or at least acted like he was.

But what could he say? He had faith that Bobby would find the counter-curse, the guy was an expert.

Which just left waiting for that call, and Dean knew with one hundred percent certainty that the best way to spend that time was _not_ pacing and worrying, which was what Sam was currently doing.

“Will you cool it, Samantha?” he sighed from his seat at the little motel table, and Sam glared daggers at him. Dean grinned, “Oh come on, for once it’s actually accurate!”

Dean’s gaze dragged purposefully down Sam’s new, very feminine body with a salacious smirk. Sam’s changed physiology meant his clothes didn’t fit very well at the moment, leaving him to pace agitatedly around the room in nothing but a t-shirt and boxers.

“I hate you,” Sam deadpanned, and Dean raised one eyebrow with a little tilt of his head.

“You’d hate me a lot less if you just came over here,” Dean purred suggestively, and Sam crossed his arms and glared, clearly not amused. Dean took full advantage of the fact that it pushed Sam’s new breasts together, accentuating them under the fabric of his shirt.

Sam realized Dean’s line of sight and dropped his arms with a huff, “Will you be serious for a second? What if I’m stuck like this?”

“You won’t be,” Dean assured him, “Bobby knows what he’s doing, he’ll find the counter-curse.”

“But what if he _doesn’t_?”

“He _will_. And anyway, what difference would it make? You’d still be a hunter, wouldn’t you? You’d still be Sammy. Just with-” he made an encompassing gesture toward his own chest, and Sam huffed, sitting down on the bed and leaning forward to rest his elbows on his knees. He ran his fingers through his hair anxiously.

“You’re not helping, dude.”

Dean sighed and stood up, coming over to the bed and kneeling in front of Sam.

“Everything is going to be fine,” he said firmly, “I promise. Meanwhile, you are truly missing out on a golden opportunity here, Sammy.”

Sam scoffed, and Dean ran his fingertips along Sam’s arms gently. He was struck by how much more… _delicate_ Sam’s hands and arms looked; not weaker, but elegant in a whole new way.

“I’m begging you, Sammy,” Dean murmured lowly, curling his hand around Sam’s smaller wrist loosely, fingertips stroking the pulse point reverently, “At least let me go down on you. You can’t have this opportunity to see what a girl orgasm feels like and not take it, man.”

He looked up to Sam’s face to find him blushing, but at least he wasn’t flat-out saying no. Dean counted the small victory.

Slowly he leaned forward, making his intentions clear and giving Sam the opportunity to pull away if he wanted to. He didn’t, and Dean placed a gentle kiss at the corner of his mouth.

Sam signed, but reached up to wrap his arms around Dean’s neck anyway, and Dean took that as his cue to give Sam a proper kiss.

“You’re such a slut,” Sam muttered, and Dean chortled.

“Duh,” he smirked, pulling back and cupping Sam’s face, “But I’m _your_ slut.”

That made Sam smile and laugh, as Dean was hoping it would, and he smiled back before leaning in for another kiss.

Dean could barely contain his excitement when Sam let him kiss down his throat, slowly coaxing him to lay back on the bed. This was hitting so many kinks he didn’t even know he had; maybe he would have to find the recipe for this particular spell.

He was too eager to spend time on the long game, so as soon as Sam was horizontal he went for the waistband of his boxers, pulling them down and off.

Sam’s breath went shallow as Dean parted his thighs, and Dean glanced up, “Y’ok, Sammy?”

“Yeah,” Sam answered quietly, and Dean stroked his hands up and down Sam’s thighs reverently, “This is just really wild.”

Dean chuckled, kissing one thigh, then the other, and Sam shifted restlessly. He kissed his way steadily higher, pressing his cock against the side of the bed for some relief.

His breath quickened as he reached Sam’s currently _very_  female parts, and he licked his lips mindlessly as the smell of arousal hit his nose. Lord knew Sam turned him on to no end in his regular, male body, but there was just something about women that pinged his primal brain hard. Combining that with Sam was just the perfect storm.

With an eager sound he spread Sam’s legs wide and lowered his head to lick Sam’s clit exploringly. Sam gasped, arching into the touch, and Dean moaned as he circled his tongue around the small bud.

Sam’s thighs flexed and shifted restlessly as Dean swirled and rubbed his tongue, cataloging all the incredible sounds Sam was making. He groaned as he ground his hips against the side of the bed, desperately turned on.

He flicked the point of his tongue rapidly against Sam’s clit as he slid a finger inside him, feeling the walls of his pussy spasm in pleasure.

“Fuck... Dean... just...” Sam panted, writhing and trembling and grasping desperately at Dean’s hair, “Fuck, just keep doing that.”

Dean obliged, pumping his finger and tonguing Sam’s clit until Sam was gasping and crying out; his whole body tensing and arching and it was _so incredibly fucking hot_.

Sam panted and whined as the crest of his orgasm broke and left him breathless and shaking on the bed, and Dean couldn’t hold out anymore. He pulled back with a ragged breath, crawling up onto the mattress with Sam and hovering over him. He undid his pants rapidly, almost in pain he was so hard, and it took only two rapid pulls on his cock for him to come, groaning and striping Sam’s stomach with hot spatters.

Sam groaned, watching Dean with half-lidded eyes. Dean rubbed hard and dirty at the head of his cock to milk every last pulse of his orgasm, looking back at Sam ravenously.

“Shit,” he panted breathlessly at the final twitch of his cock, bracing forward on one arm against the bed, his head hanging low and his sticky cock still in his hand, “Fucking...”

“Yeah,” Sam agreed, and suddenly burst out in a breathless laugh.

“What?” Dean frowned, lifting his head to give Sam a confused look.

“Nothing,” Sam grinned, “It’s just... I think I get why girls were always so loathe to see you go in the morning.”

Dean barked out a surprised, breathless laugh, and Sam grinned wider. They suddenly found themselves giggling and laughing ridiculously, and Dean was almost lightheaded he felt so good.

He went willingly and eagerly when Sam reached up and pulled on his shoulders, coaxing him down to lay over Sam warmly.

Selfishly, he hoped that Bobby wouldn’t find the counter-curse until at least tomorrow.

Somehow he didn’t think Sam would mind.

**Notes for the Chapter:**

> It occurs to me that this is remarkably similar to my other gender-bent Supernatural fic [Magic](http://archiveofourown.org/works/1027944), just with which character is being gender-bent reversed. Oh well. Still fun, I think.


	24. X = X-Ray

Dean’s no slouch. He doesn’t have a porn star dick or anything, but he’s a decent bit above the national average, on all accounts.

Far more important, in his opinion, is what he can do with it. That stupid saying about “not the size of the boat, it’s the motion of the ocean” may be something people say to insecure guys, but there was a foundation of truth in it. Having a a nice cock but not knowing what you’re doing with it was just as much of a waste, in his opinion.

Which is why he made every sexual encounter throughout his teen years a learning experience. Also why he preferred dominant women; they weren’t afraid to tell him what they wanted, and he was constantly thrilled to do it for them.

He wasn’t any different in his approach when it came to Sam, either. He wasn’t sure what stroke of luck enabled him and Sam to be so perfectly compatible, but the fact that Sam liked to call the shots in bed while Dean liked being told what to do was just eerily perfect.

Speaking of perfect, no one would ever offer the “motion of the ocean” platitude to Sam. Not only was Sam’s dick proportionally big to suit his giant body, but he had spent his time in college learning a few tricks, it seemed.

The first time he let Sam fuck him, it started off awkward and nervous; he’d had a few kinky chicks in his past who had been into butt stuff, and he’d even allowed a girl to peg him on one memorable occasion. (It was embarrassing how much it had turned him on), but it was different with Sam. Not just because he was bigger than that toy had been, but because as much as Sam was pushy in bed, he was also extremely sensitive and attuned to Dean, and all of his stupid insecurities.

By the time he convinced Sam that, yes, this actually would go a lot smoother if you just went for it instead of constantly asking if I’m okay, Dean was starting to give up hope that the night would be anything other than a disaster. Thankfully, Sam eventually took Dean at his word and just acted. Dean decided right then and there that he was never taking Sam’s hands for granted again, and an hour later he was making the same pledge to himself about Sam’s cock.

Not that he’d ever expressly say that to Sam, of course. Couldn’t risk the kid’s ego getting too inflated. Sam would just have to be satisfied with Dean’s blissed-out orgasm coma, that’s all.

That was fine, though. They were even, in that regard; Dean took personal, deep delight in reducing Sam to a quivering mess in turn, so it all worked out. Dean was no slouch, and Sam was his favorite person to prove it to.


	25. Y = Yearning

“ _Again?_ ” Sam sighed into his pillow, and Dean smirked against his shoulder, where he was laying a leisurely trail of kisses. His cock was also rubbing against the side of Sam’s hip, but that was neither here nor there.  


“What’s the matter, Sammy? Ain’t got the stamina?” Dean teased, biting Sam’s shoulder gently, and Sam snorted.  


“I am four years younger than you, you know,” Sam reminded him, “Stamina is not my issue. You’re just an insatiable slut.”  


“Damn straight,” Dean grinned, “So are you gonna fuck me, or not?”

Sam chuckled, rolling onto his side and pulling Dean against him. He sought Dean’s mouth in the dark room, and Dean went into the kiss eagerly.

He hummed at Sam’s hand trailed down his back and to his ass, squeezing firmly before pressing a finger between his cheeks. Dean hiked his leg over Sam’s hip, giving him better access, and Sam chuckled softly.

“Slut,” Sam sighed again, pressing his finger against Dean’s still lube and cum-slick hole.  


“You love it,” Dean whispered back with a smile, and Sam laughed breathily.  


“Lucky you,” he said dryly, pushing a finger in and Dean gasped. He pressed forward against Sam’s pelvis, rubbing his hard on against the sharp cut of muscle.  


“I don’t even have to do this, do I?” Sam murmured, his lips trailing down Dean’s chin and to his throat, “I could fuck you right now and you’d beg me for more.”  


Dean moaned, his cock jerking against Sam’s hot skin. Sam was getting hard now too, Dean could feel it against his hip and he reached a hand down to help Sam along.

Sam hummed encouragingly at Dean’s touch, nipping at Dean’s neck gently.

“On your belly,” Sam instructed softly, and Dean eagerly shifted around until he was laying on his stomach, Sam sliding over him from behind. He humped against the sheets, the friction against the head of his cock sending sparks of pleasure up his spine.  


He could hear Sam stroking himself as he pushed two fingers back into Dean, making Dean whimper and squirm against the pressure.

“So pretty, Dean,” Sam murmured, leaning down to kiss his back, and Dean chortled.  


“Don’t be a sap, Sammy,” he gasped as Sam pressed hard against his prostate, and a blurt of precome dampened the sheets below him.  


Sam shook his head with a little chortle, continuing to kiss Dean’s back and rubbing his fingers against Dean’s sweet spot again, making Dean jerk.

“Fine, I won’t compliment you, I’ll just fuck you instead,” Sam said, “How’s that?”  


“Get to it, baby,” Dean smirked, and Sam chuckled, giving Dean’s ass a little smack before he laid over him, rubbing his cock between Dean’s cheek slowly.

“You’re ridiculous,” Sam mumbled against his shoulder, but any snappy retort Dean was ready to throw back at him was cut off by Sam guiding his cock inside him in one firm stroke.  


Dean shuddered with pleasure, groaning as Sam started thrusting slow and deep. Dean reached one hand behind his head to slide his fingers into Sam’s hair, and the other down to Sam’s thigh, encouraging the steady push of his hips.

It was slow and sensual, and Dean shuddered and moaned as the push of Sam’s cock against his sweet spot and the rub of Dean’s cock against the sheets started a slow build of pleasure in him. He gave himself over to it, panting against the pillow and pushing back and forth between Sam’s hips and the bed.

Sam kissed and bit along Dean’s shoulders lightly, breathing warm and soft against Dean’s skin. It was intimate in a way that he would never want to admit to loving, and a little moan of pleasure escaped Sam’s lips.

Slow and steady as a heart beat, Dean’s pleasure mounted and higher and higher until it broke over him like a wave and he came, holding tight to Sam as he shook and panted.

Sam grunted as his hips picked up speed, driving in fast and deep until he came as well, groaning into the back of Dean’s neck.

They panted quietly together, Sam still draped along Dean’s back and his mouth running aimlessly along his skin. Eventually he rolled to the side, pushing his hair out of his face as Dean wiggled out of the wet spot with a little grunt.

“Happy now?” Sam asked, and Dean could hear the smile in his voice.  


“For now,” he said cheekily, and Sam chortled.

“Ridiculous,” Sam sighed, starting to doze off, and Dean grinning against the pillow.  


“Night, Sammy.”  



	26. Z = Zzz...

Dean had always been quick to fall asleep, in general. The hunting life had conditioned him to be able to; crazy nights and days of research and literal fighting for your life meant that you grabbed sleep when you could, because you didn’t know when the opportunity would come again.

Sex wasn’t really a different story, he was a little ashamed to admit. It’s not like he rolled off his partner and immediately was down for the count or anything, but the cozy, post-coital cuddling never failed to lull him off to sleep in five minutes or less.

There was something particularly addictive about sleeping with his brother, especially. He didn’t fall asleep any quicker or slower after sex with Sam, but when he did sleep it was always more restful, more peaceful. The nightmares were fewer and farther between, and his body felt better and more relaxed upon waking the next morning.

This feeling was doubled once they found the bunker. Being somewhere that they could lock down, was warded, secret, secure. That gave him peace of mind that he had never felt before, and it was reflected in how deeply he slept.

Sam might try to play it cool, and act like the bunker wasn’t affecting him the same way, but Dean could see that was a big fat lie. The number of times he’d rescued an antique book from falling out of Sam’s limp hand after the giant goof fell asleep on one of the library’s couches was proof enough of that.

And it’s proof enough now, watching Sam sleep in their bed, cuddling Dean’s pillow in his brother’s absence. They had sex a few hours ago, in the middle of the afternoon, just because they could. But unlike Sam, Dean’s growling stomach was enough to propel him out of bed and into the kitchen to make them some dinner.  


Dean leaned against the door frame, listening to the slow, steady sound of Sam’s breathing and watching his brother’s serene face. He almost didn’t want to wake him; he just wanted nothing more than for Sammy to feel as safe and relaxed as he did right now.

In the end, he didn’t have to, as Sam took a deep breath and his eyes fluttered open. He squinted slightly, and his gaze fell on Dean.

“You bein’ a creep an’ watchin’ me sleep?” Sam murmured lowly, and Dean smiled.  


“Maybe,” he said vaguely, and Sam chortled.  


“Weirdo.”  


Dean said nothing as Sam stretched, raising his arms above his head and flexing his whole body. Dean’s eyes trailed down over Sam’s exposed muscles greedily.

“You cookin’ dinner? Something smells good,” Sam asked, eyes closed, and Dean grunted in the affirmative.  


“Cool. Thanks,” Sam sighed, and Dean shook his head. Sam was halfway back to sleep already, and the temptation to join him was strong.  


Instead, he moved toward the bed and placed a gentle kiss to Sam’s forehead.

“Want me to wake you when it’s done? Shouldn’t be too much longer.”  


“Ok,” Sam whispered sleepily, and Dean smiled before pressing another kiss to Sam’s head, “Love you, Dean.”  


“Love you too, Sammy.”

**Notes for the Chapter:**

> Holy crap, guys, this is it! This is the end! I’m finally _finally_  done with this challenge! It took me way longer than I would have liked, (sorry about that) but it’s finally complete, and ending on a totally and ridiculously sappy note. I really hope y'all enjoyed it!


End file.
